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PubMed1996

Evaluation of the potential carcinogenic activity of Senna and Cascara glycosides for the rat colon.

Anthraquinone glycosides of Senna and Cascara were investigated for their ability to induce aberrant crypt foci (ACF) in the rat colon mucosa, which are considered putative preneoplastic lesions. Dietary exposure to high doses of these glycosides for 56 successive days did not cause the appearance of ACF or increase in incidence of ACF induced by 1,2-dimethyl-hydrazine (DMH). However, in rats treated with both DMH and the highest dose of glycosides, the average number of aberrant crypts per focus, considered a consistent predictor of tumor outcome, was higher than in rats given DMH alone. These findings suggest that Senna and Cascara glycoside might behave as weak promoters in rat colon carcinogenesis.

Animals↗
PubMed1996

Role of endogenous cardiac glycosides in the spontaneously hypertensive rat--antagonism by active immunization.

The effects of simultaneous active immunization against two cardiac glycoside drugs, digoxin and proscillaridin, have been examined in young spontaneously hypertensive and Wistar-Kyoto rats. Control animals were immunized with protein carrier only. Animals were studied from 5 weeks to 13 weeks of age. Effectiveness of immunization to produce antibody responses was assessed at the end of the study by estimating the titer of antibodies in plasma against both of the antigens. Robust antibody responses were obtained. Immunization had no effect on the normal growth of these animals. Further, immunization against cardiac glycosides did not change blood pressure in either strain of animals. Blood pressure in the SHR increased as anticipated as the weanling animals grew to maturity. These studies indicate that active immunization against cardiac glycosides does not alter blood pressure in the SHR in spite of strong evidence for increased levels of endogenous cardiac glycosides in this strain.

Animals↗
PubMed2002

4'-deoxy iridoid glycosides from Centranthus longiflorus.

The new iridoid glycosides, 4'-deoxykanokoside A and 4'-deoxykanokoside C, were isolated from the methanolic root extract of Centranthus longiflorus ssp. longiflorus. They were accompanied by the three known iridoid glycosides, kanokoside A, kanokoside C and valerosidatum, and two known phenylpropanoid glycosides, coniferin and isoconiferinoside. The structures were elucidated mainly by spectroscopic methods. The presence of 4-deoxy glucose as a part of plant glycosides is rather unusual. Cytotoxic effects of the isolated compounds were also investigated.

Iridoids↗
PubMed1998

New glycosides from ajuga decumbens

A new phenethyl alcohol glycoside, galactosylmartynoside (1), and a new abietatriene-type diterpene glycoside, ajugaside A (2), were isolated from the whole plants of Ajuga decumbens, together with known phenethyl alcohol glycosides (3 and 4) and iridoid glycosides (5-7). Chemical structures were elucidated on the basis of spectral data. Of these compounds, 8-acetylharpagide (6) exhibited the strongest inhibitory effect on Epstein-Barr virus activation induced by 12-O-tetradecanoylphorbol-13-acetate.

Journal Article↗
PubMed1968

Nature of the Schwann cell electrical potential. Effects of the external ionic concentrations and a cardiac glycoside.

The effects on the Schwann cell electrical potential of external ionic concentrations and of K-strophanthoside were investigated. Increasing (K)(o) depolarized the cell. The potential is related to the logarithm of (K)(o) in a quasi-linear fashion. The linear portion of the curve has a slope of 45 mv/ten-fold change in (K)(o). Diminutions of (Na)(o) and (Cl)(o) produced only small variations in the potential. Calcium and magnesium can be replaced by 44 mM calcium without altering the potential. Increase of (Ca)(o) to 88 mM produced about 10 mv hyperpolarization. The cell was hyperpolarized by 11 mv and 4 mv within 1 min after applying K-strophanthoside at concentrations of 10(-3) and 10(-5)M, respectively. No variations of cellular potassium, sodium, or chloride were observed 3 min after applying the glycoside. The hyperpolarization caused by 10(-3)M K-strophanthoside was not observed when (K)(o) was diminished to 1 or 0.1 mM or was increased to 30 mM. At a (K)(o) of 30 mM, 10(-2)M strophanthoside was required to produce the hyperpolarizing effect. In high calcium, the cell was further hyperpolarized by the glycoside. The initial hyperpolarization caused by the glycoside was followed by a gradual depolarization and a decrease of the cellular potassium concentration. The results indicate that the Schwann cell potential of about -40 mv is due to ionic diffusion, mainly of potassium, and to a cardiac glycoside-sensitive ion transport process.

Animals↗
PubMed1983

The cardiac glycoside-receptor system in the human heart.

Specific binding sites have been demonstrated to exist in the heart for several drugs and hormones such as beta-blocking agents, cardiac glycosides, catecholamines, insulin, glucagon and acetylcholine. The specific binding sites for cardiac glycosides in the human heart have certain properties which make it likely that they are the pharmacological receptors for the therapeutic and toxic actions of digitalis glycosides: they are located in the cell membrane and bind cardioactive steroids reversibly with high affinity: half-maximal receptor binding occurs at approximately 2 nM (approximately 1.5 ng/ml) for digoxin; potassium decreases receptor affinity, calcium increases it; specific binding of ouabain, digoxin or digitoxin is related to inhibition of (Na+ + K+)-ATPase activity--which is supposed to be the receptor enzyme for cardiac glycosides. Human left ventricle contains approximately 1.5 x 10(14) binding sites/g wet weight, right ventricle approximately 0.9 x 10(14). In disease the number of receptors may decrease (hypothyroid states, myocardial infarction) or increase (hyperthyroidism, chronic hypokalaemia). Certain drugs (such as phenytoin) or different temperatures or pH changes cause a change in digitalis-receptor affinity. Thus, the number of receptors and possibly their properties are subject to regulation in clinically relevant situations. Further investigations will probably reveal those pathophysiological states, which allow the explanation of toxicity or digitalis refractoriness.

Animals↗
PubMed2003

The bioavailability of quercetin in pigs depends on the glycoside moiety and on dietary factors.

Recent investigations suggest that the bioavailability of quercetin depends on the glycoside moiety of the quercetin glycosides present in the diet. In this study, we compared the oral bioavailability of quercetin from quercetin aglycone and two different quercetin glycosides in pigs. Pigs were equipped with permanent catheters in the jugular and portal veins. After consumption of a test meal containing the respective compounds, blood samples were drawn repeatedly over a period of 24 h and analyzed by HPLC. In a first set of experiments, pigs received a single oral dose of 148 micromol/kg body (equivalent to 50 mg/kg) provided as quercetin aglycone, quercetin-3-O-glucoside (Q3G) or quercetin-3-O-glucorhamnoside (rutin) as part of their diet. The main metabolite in plasma was always conjugated quercetin, whereas free quercetin was not detected in either the jugular or the portal blood. For Q3G and rutin, the relative total bioavailability of quercetin (i.e., conjugated quercetin and conjugated methylethers of quercetin) was 148% (P = 0.07) and 23% (P < 0.05), respectively, compared with quercetin aglycone. In another experiment with a dose of 29.6 micro mol/kg (equivalent to 10 mg/kg), the relative total bioavailability of Q3G was 167% compared with the aglycone (P < 0.05). Bioavailability of Q3G was significantly higher when the test meal was ground beef rather than the standard ration. Our results indicate that the bioavailability of quercetin from quercetin glycosides is determined by a complex interdependence between the chemical form of the flavonols and dietary factors.

Animals↗
PubMed2006

The inhibitory effect of phenylpropanoid glycosides and iridoid glucosides on free radical production and beta2 integrin expression in human leucocytes.

Rapid production of reactive oxygen species (ROS) and upregulation of beta2 integrin by leucocytes are two important inflammatory responses in human leucocytes. To evaluate whether three phenylpropanoid glycosides (acteoside, crenatoside, and rossicaside B) and two iridoid glucosides (boschnaloside and 8-epideoxyloganic acid) identified from two medicinal plants with similar indications (Orobanche caerulescens and Boschniakia rossica) exhibited anti-inflammatory activity, their effects on N-formyl-methionyl-leucyl-phenylalanine (fMLP) and phorbol-12-myristate-13-acetate (PMA)-activated peripheral human neutrophils (PMNs) and mononuclear cells were examined. Pretreatment with 1-50 microM phenylpropanoid glycoside concentration-dependently diminished PMA- and fMLP-induced ROS production with IC50 values of approximately 6.8-23.9 and 3.0-8.8 muM, respectively. Iridoid glucoside was less effective than phenylpropanoid glycoside with an IC50 value of approximately 8.9-28.4 microM in PMA-activated PMNs and 19.1-21.1 microM in fMLP-activated mononuclear cells. Phenylpropanoid glycosides also effectively inhibited NADPH oxidase (NOX) and displayed potent free radical-scavenging activity, but did not interfere with pan-protein kinase C (PKC) activity. Furthermore, all compounds, except rossicaside B, significantly inhibited PMA- and fMLP-induced Mac-1 (a beta2 integrin) upregulation at 50 microM but not that of fMLP-induced intracellular calcium mobilization. These drugs had no significant cytotoxicity as compared with the vehicle control. Our data suggested that inhibition of ROS production, possibly through modulation of NOX activity and/or the radical scavenging effect, and beta2 integrin expression in leucocytes indicated that these compounds had the potential to serve as anti-inflammatory agents during oxidative stress.

Anti-Inflammatory Agents, Non-Steroidal↗
PubMed2004

Effects of iridoid total glycoside from Cornus officinalis on prevention of glomerular overexpression of transforming growth factor beta 1 and matrixes in an experimental diabetes model.

The present study was conducted to determine whether iridoid total glycoside from Cornus officinalis was effective in regulating expression of transforming growth factor beta 1 (TGF-beta1) and preventing overdeposition of extracellular matrix (ECM) in a diabetes state. An experimental rat model of diabetic nephropathy (DN) was successfully induced by one intraperitoneal injection of streptozotocin at a dose of 60 mg x kg(-1) and maintained for 12 weeks. All rats had free access to standard chow and water. Four groups: normal control, diabetic control, diabetic rats with aminoguanidine treatment and diabetic rats with iridoid total glycoside treatment were used in this experiment. All treatments were administered by intragastric gavage (ig). At the end of the experiment, serum was collected for ELISA determination of TGF-beta1 protein level; renal cortex was dissected for reverse transcription polymerase chain reaction (RT-PCR) analysis of its mRNA expression; and immunohistochemistry was introduced to observe ECM deposition. A significantly higher level of protein and mRNA expression of TGF-beta1, and also overdeposition of fibronectin and laminin was found in diabetic rats. Both iridoid total glycoside and aminoguanidine were effective in decreasing serum protein level and glomerular mRNA expression of TGF-beta1, and in preventing renal overdeposition of fibronectin and laminin. This study suggests that iridoid total glycoside is a beneficial agent for prevention and therapy of DN.

Animals↗
PubMed2003

Syntheses of arbutin-alpha-glycosides and a comparison of their inhibitory effects with those of alpha-arbutin and arbutin on human tyrosinase.

The effects of 4-hydroxyphenyl alpha-glucopyranoside (alpha-arbutin) and 4-hydroxyphenyl beta-glucopyranoside (arbutin) on the activity of tyrosinase from human malignant melanoma cells were examined. The inhibitory effect of alpha-arbutin on human tyrosinase was stronger than that of arbutin. The K(i) value for alpha-arbutin was calculated to be 1/20 that for arbutin. We then synthesized arbutin-alpha-glycosides by the transglycosylation reaction of cyclomaltodextrin glucanotransferase using arbutin and starch, respectively, as acceptor and donor molecules. The structural analyses using 13C- and 1H-NMR proved that the transglycosylated products were 4-hydroxyphenyl beta-maltoside (beta-Ab-alpha-G1) and 4-hydroxyphenyl beta-maltotrioside (beta-Ab-alpha-G2). These arbutin-alpha-glycosides exhibited competitive type inhibition on human tyrosinase, and their K(i) values were calculated to be 0.7 mM and 0.9 mM, respectively. These arbutin-alpha-glycosides possessed stronger inhibitory activity than arbutin, but less activity than alpha-arbutin. These results suggested that the alpha-glucosidic linkage of hydroquinone-glycosides plays an important role in the inhibitory effect on human tyrosinase.

Arbutin↗
PubMed1991

[Simultaneous determination of five bitter secoiridoid glycosides in nine Chinese Gentiana species used as the Chinese drug "long dan" by high performance liquid chromatography].

A new and rapid analytical method for the simultaneous determination of five bitter secoiridoid glycosides (gentiopicroside, GTP; swertiamarin, SWT; sweroside, SWO; amarogentin, AMG; amaroswerin, AMS) in the Chinese drug "Long Dan", roots of Gentiana manshurica and 8 allied species by high performance liquid chromatography (HPLC) has been developed. The HPLC system consisting of an apparatus from Shimadzu (model LC-4A), with a UV-detector (SPD-2AS), a data processor (Chromatopac C-R2AX), a column oven (CTO-2AS), and a Zorbax ODS column (25 cm x 4.6 mm ID) was used. Using MeOH--H2O as the mobile phase, the linear concentration-program of methanol was [time (min):C (MeOH)]: [0:20]----[6:20]----[6.01:40]----[23:stop]. The temperature of column oven was 40 degrees C. The bitter secoiridoid glycosides eluted were detected at a wavelength of 254 nm and the analysis was successfully carried out within 23 minutes. This method is sensitive, rapid, accurate and has good reproducibility. Recoveries of each secoiridoid glycoside were 100.0-101.5% with coefficients of variation 0-2.5% (n = 3). The contents of five bitter secoiridoid glycosides in the roots of G. manshurica and eight allied species indigenous to China were determined and reported.

Chromatography, High Pressure Liquid↗
PubMed1990

[Application of 13CNMR to structural identification of the flavonoid glycosides].

13CNMR has become an important method for the structural determination of organic natural products. It is especially useful for identifying the structure of glycosides. This paper deals with the application of 13CNMR to the identification of the flavonoid glycosides isolated from the roots of Glycyrrhiza eurycarpa P.C. Li. The discrimination of chemical shifts of C-2, C-3 and C-4 (carbonyl) signals for different types of flavonoids, such as isoflavones, flavanones, chalcones, flavones and pterocarpans is discussed. The application of 13CNMR in the determination of structure and configuration of sugar moieties, for determination of glycosidic linkage, and for confirmation of the position of glycosidation and linkage between two sugar moieties are also discussed briefly.

Carbon Radioisotopes↗
PubMed1988

Effect of the N-glycosidic bond conformation and modifications in the pentose moiety on the binding of nucleoside ligands to uridine phosphorylase.

Several arabinosyl-, xylosyl-, lyxosyl, 5'-deoxy-, acyclo-, 2,2'-anhydro-, 2,3'-anhydro-2'-deoxy-, 2,5'-anhydro-, 6,5'-cyclo-, and carbocyclic analogues of uridine with various 5-substitutions (fluoro, methyl, bromo, ethyl, benzyl, or benzyloxybenzyl) have been tested and compared with their corresponding ribo- and 2'-deoxyribosides for their potency to inhibit uridine phosphorylase (UrdPase) from both mouse and human livers. The effect of the alpha- and beta-configurations of the glycosidic bond was also tested. Xylo-, lyxo-, 2,3'-anhydro-2'-deoxy-, 6,5'-cyclo-, and carbocyclic uridines did not bind to the enzyme. Ribosides bound better than the corresponding 2'-deoxyribosides, which were better than the 5'-deoxyribosides. 2'-alpha-Deoxyribosides bound to the enzyme, albeit less tightly than the corresponding beta-anomers. The acyclo- and 2,2'-anhydrouridines were all potent inhibitors with the 2,2'-anhydro- derivatives being the most potent. 2,5'-Anhydrouridine bound to UrdPase less effectively than 2,2'-anhydrouridine and acyclouridine. Arabinosyl uracil was at best a very poor inhibitor but binds better if a benzyl group is added at the 5-position of the pyrimidine ring. This binding was enhanced further by adding a 5-benzyloxybenzyl group. A similar enhancement of the binding with increased hydrophobicity at the 5-position of the pyrimidine ring was observed with ribosides, alpha- and beta-anomers of the 2'-deoxyribosides, acyclonucleosides, and 2,2'-anhydronucleosides. The inhibitory potencies of these compounds with UrdPase from human liver roughly parallel those obtained with UrdPase from mouse liver. It is concluded that the presence of a N-glycosidic bond as well as a properly oriented 3'-hydroxyl group are prerequisites for a nucleoside ligand to bind to UrdPase. On the other hand, the presence of a 2'- or 5'-hydroxyl group or an N-glycosidic bond in the beta-configuration enhances but is not essential for binding. Furthermore, the potency of the binding of 2,2'-anhydrouridines (fixed syn-isomers) in contrast to the complete lack of binding of the 6,5'-cyclouridines (fixed anti-isomers) to UrdPase indicates that the binding of ligands to this enzyme is in the syn-conformation around the N-glycosidic bond.

Isomerism↗
PubMed1978

Cardiac effects of 16-acetyl-gitoxin, the active glycoside after penta-acetyl-gitoxin administration.

The inotropic and arrhythmogenic effects of 16-acetyl-gitoxin and digoxin were studied in isolated cardiac preparations and in anaesthetized dogs. ECG alteration-producing and lethal doses of both glycosides were determined in anaesthetized cats. In the isolated guinea-pig atrium, the properties of 16-acetyl-gitoxin are identical with those of ouabain, and in the isolated guinea-pig heart they are equal to those of digoxin, while gitoxin and penta-acetyl-gitoxin produce equieffective reactions at higher glycoside concentrations. In the cat, 75% of lethal doses of 16-acetyl-gitoxin and digoxin provoke ECG changes (qrs complex prolongation). The ratio of the lethal doses amounts to 1:2.8 and 1:3.5 (digoxin:16-acetyl-gitoxin). In case of equal contractile increment, the ratio of glycoside doses in dogs amounts to 1:1.3, while the percentages of rhythm disturbances following both glycosides are identical. Apart from slight deviations of the doses used, the cardiac properties of 16-acetyl-gitoxin are equal to those of digoxin.

Acetyldigoxins↗
PubMed2000

Regioselectivity of enzymatic glycosylation of 6-O-acyl glycosides in supersaturated solutions.

The regioselectivity of enzymatic transglycosylation of 6-O-acetyl glycosides in supersaturated solutions was investigated using a range of commercially available enzymes, Escherichia coli, barley, and Kluyveromyces spp. beta-galactosidase, green coffee bean alpha-galactosidase, jack bean alpha-mannosidase, rice alpha-glucosidase, and almond beta-glucosidase. It has been shown that 6-O-acetyl glycosides serve as good substrates for these enzymes, which, under the reaction conditions, are "forced" to transfer monosaccharide units to the secondary hydroxyl groups of the acceptors. In a variety of transglycosylations studied the (1-3)-linked disaccharide products were the predominant regioisomers isolated. The selectivity of the reaction varied significantly depending on the acceptor glycosides and the enzyme used. Exquisite specificity was observed in some cases, but in others approximately equal quantities of two disaccharides products were isolated. In the best transfers the yield approached 30%. The methodology described offers a quick and facile route to disaccharides that may be difficult and/or time consuming to make by conventional chemical synthesis.

Carbohydrate Conformation↗
PubMedDate not supplied

The current concept for the cardiac glycoside receptor.

This brief review emphasizes the significance of the Na+,K+-ATPase or the Na+,K+ pump of the intact membrane as the pharmacological receptor for cardiac glycosides. The properties of transport enzyme and the regulation of glycoside binding are described. An outline is given of the problems encountered and of the progress made in attempting to correlate the inotropic action of cardiac glycosides with the binding of these drugs to the heart muscle and with the inhibition of the Na+,K+ pump. Furthermore, the correlation of intracellular Ca2+ activity an Na+ concentration with the inhibition of the Na+,K+ pump is discussed. The existence of a digitalis-like endogenous activity may also indicate an important role of the Na+,K+ pump as a receptor for a physiological regulatory control of cardiac contractility.

Cardiac Glycosides↗
PubMed1986

Cellular basis for the species differences in sensitivity to cardiac glycosides (digitalis).

The relative toxicity of numerous cardiotonic steroids (viz. ouabain, digitoxin, digoxin, convallatoxin, SC4453, bufalin, gitaloxin, digoxigenin, actodigin, oleandrin, digitoxigenin, gitoxin, strophanthidin, gitoxigenin, lanatosides A, B and C, alpha- and beta-acetyl digoxin, alpha- and beta-methyl digoxin) and related compounds towards a number of independent cell lines established from human, monkey, mouse, Syrian hamster, and Chinese hamster have been determined. All cardiac glycosides and their genins, as well as the cardiotonic alkaloid cassaine, exhibited greater than 100-fold higher toxicity towards cultured human and monkey cells in comparison to the cell lines of mouse, Syrian hamster, and Chinese hamster origins. These differences are species-related as all cell lines (both normal as well as transformed) from any one species, as well as cells from the closely related species (e.g., man and monkey or mouse, Chinese hamster, and Syrian hamster), showed similar sensitivity towards these drugs. The failure to see any significant differences in cellular toxicity for a larger number of other compounds which either bear limited structural resemblance to cardiac glycosides (viz. estradiol 17-beta-acetate, testosterone propionate, 21-acetoxy pregnenolone, beta-estradiol, digitonin, tigogenin, and tomatine) or interact with the Na+/K+ ATPase in a different manner (viz. veratridine, sanguinarine nitrate, penicillic acid, vanadium pentoxide, harmaline-HCI,5,5'-diphenyl hydantoin, quindonium bromide, and methyl quinolizinum bromide) provides strong evidence that the observed species-related differences are highly specific for cardiotonic steroids. Studies on the binding of [3H]ouabain show that, in comparison to human and monkey cell lines, no significant binding of the drug is observed in cells derived from the resistant species (i.e., mouse and Chinese hamster). The Na+/K+ ATPase from cells of the resistant species is inhibited at much higher concentrations of ouabain and digitoxin in comparison to the enzyme from human cells, and a good correlation is observed between these concentrations and those reported for inhibition of the enzyme from isolated heart muscles of the same species. These results provide strong evidence that the species-related differences in sensitivity to digitalis have a cellular basis and that the cultured cells from various mammalian species provide a useful model system for investigating the mechanism of action of cardiac glycosides.

Animals↗
PubMed1986

3-Methoxy-4-(2-nitrovinyl)phenyl glycosides as potential chromogenic substrates for the assay of glycosidases.

Selective glycosidation of 2,4-dihydroxybenzaldehyde with either 2,3,4, 6-tetra-O-acetyl-alpha-D-glucopyranosyl bromide, 2-acetamido-3,4,6-tri-O-acetyl-alpha-D-glucopyranosyl chloride, or 2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosyl bromide afforded the corresponding 4-O-glycosyl derivatives. Subsequent O-methylation, O-deacetylation, and condensation with nitromethane afforded the appropriate beta-glycoside of 3-methoxy-4-(2-nitrovinyl)phenol. The phenol is highly coloured at alkaline pH so that these glycosides may be suitable as chromogenic substrates for the assay of glycosidases.

Chemical Phenomena↗